This invention relates to certain oxazines and thiazines, including all geometric and stereoisomers, agriculturally-suitable salts thereof, agricultural compositions containing them and their use as arthropodicides in both agronomic and nonagronomic environments.
WO 94/14783 discloses pesticidal 2-phenyl-1,3-oxazine or 1,3-thiazine derivatives of the following general formula: ##STR2## wherein: Z is O or S;
Y is halogen, NO.sub.2, CN, or optionally substituted alkyl, alkoxycarbonyl, alkoxy or amino, or S(O).sub.p r.sup.1 ; PA1 p is 0-2; PA1 m is 1-3; PA1 r.sup.1 is optionally substituted alkyl; PA1 R.sub.1, R.sub.2 and R.sub.4 are H or optionally substituted alkyl or phenyl; PA1 R.sub.3 is alkyl, alkenyl, aralkyl, cycloalkyl, phenyl, naphthyl, pyridyl, furyl or thienyl, all optionally substituted by halogen, OH, alkyl, cycloalkyl, phenyl, alkoxy, phenoxy, heterocyclyl, heterocyclyloxy, alkylthio, phenylthio or amino, which may be further substituted. PA1 Q is selected from the group phenyl, pyridyl, thienyl, furyl and naphthyl, each ring substituted with R.sup.3, R.sup.4 and R.sup.5 ; PA1 E is selected from the group C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 haloalkyl; PA1 Z is selected from the group O and S; PA1 R.sup.1 and R.sup.2 are independently selected from the group H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, CN and NO.sub.2 ; PA1 R.sup.3 is selected from the group C.sub.1 -C.sub.10 alkyl substituted with at least one member independently selected from the group CN, NO.sub.2, Si(R.sup.6)(R.sup.7)(R.sup.8), C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 haloalkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, and C.sub.2 -C.sub.6 haloalkoxycarbonyl; C.sub.2 -C.sub.6 alkylcarbonyl; C.sub.2 -C.sub.6 haloalkylcarbonyl; C.sub.2 -C.sub.6 alkoxycarbonyl; C.sub.2 -C.sub.6 haloalkoxycarbonyl; C.sub.2 -C.sub.10 alkenyl optionally substituted with at least one member independently selected from R.sup.9 ; C.sub.2 -C.sub.10 alkynyl optionally substituted with at least one member independently selected from R.sup.9 ; C(O)R.sup.14 ; C(O)OR.sup.14 ; C(O)N(R.sup.10)R.sup.11 ; OR.sup.12 ; --C(R.sup.10)=N--OR.sup.11 ; --O--N=C(R.sup.10)(R.sup.11); phenyl substituted with at least one member independently selected from W.sup.1 ; and an 8- to 12-membered fused bicyclic ring system containing 0-4 heteroatoms independently selected from 0-4 nitrogen, 0-2 oxygen and 0-2 sulfur, the ring system optionally substituted with at least one member independently selected from W; PA1 R.sup.4 and R.sup.5 are independently selected from the group H, halogen, CN, NO.sub.2, C.sub.1 -C.sub.16 alkyl, C.sub.1 -C.sub.16 alkoxy, C.sub.1 -C.sub.16 haloalkyl, C.sub.1 -C.sub.16 haloalkoxy, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.16 cycloalkylalkyl, C.sub.2 -C.sub.16 alkenyl, C.sub.2 -C.sub.16 haloalkenyl, C.sub.2 -C.sub.16 alkynyl, C.sub.2 -C.sub.16 haloalkynyl, C.sub.2 -C.sub.16 alkoxyalkoxy, and phenyl optionally substituted with at least one member independently selected from W; PA1 R.sup.6 and R.sup.7 are independently selected from the group C.sub.1 -C.sub.6 alkyl; PA1 R.sup.8 is selected from the group C.sub.1 -C.sub.6 alkyl and phenyl optionally substituted with W; PA1 R.sup.9 is selected from the group halogen, CN and Si(R.sup.6)(R.sup.7)(R.sup.8); or R.sup.9 is selected from the group phenyl and pyridyl, each optionally substituted with at least one member independently selected from W; PA1 R.sup.10 and R.sup.11 are independently selected from the group H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, phenyl optionally substituted with at least one member independently selected from W, and benzyl optionally substituted with at least one member independently selected from W; PA1 R.sup.12 is selected from the group tetrahydropyranyl; C.sub.1 -C.sub.10 alkyl substituted with at least one member independently selected from the group CN, Si(R.sup.6)(R.sup.7)(R.sup.8), C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 haloalkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl and C.sub.2 -C.sub.6 haloalkoxycarbonyl; C.sub.2 -C.sub.10 alkenyl optionally substituted with at least one member independently selected from the group halogen, CN and C.sub.2 -C.sub.6 alkoxycarbonyl; C.sub.3 -C.sub.7 cycloalkyl; C.sub.3 -C.sub.7 halocycloalkyl; C.sub.4 C.sub.7 cyanocycloalkyl; C.sub.4 -C.sub.7 alkylcycloalkyl; C.sub.4 -C.sub.7 cycloalkylalkyl; C.sub.4 -C.sub.7 halocycloalkylalkyl; and an 8- to 12-membered fused bicyclic ring system containing 0-4 heteroatoms independently selected from 0-4 nitrogen, 0-2 oxygen and 0-2 sulfur, the ring system optionally substituted with at least one member independently selected from W; PA1 R.sup.13 is selected from the group C.sub.1 -C.sub.3 alkyl and C.sub.1 -C.sub.3 haloalkyl; PA1 R.sup.14 is selected from the group phenyl and pyridyl, each optionally substituted with at least one member independently selected from W; PA1 W is selected from the group halogen, CN, CHO, NO.sub.2, SF.sub.5, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy, C.sub.2 -C.sub.4 alkylcarbonyl and C.sub.2 -C.sub.4 alkoxycarbonyl; PA1 W.sup.1 is selected from the group CN, CHO, NO.sub.2, SF.sub.5, S(O).sub.n R.sup.13, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl, --C(R.sup.10)=N--OR.sup.11 and --O--N=C(R.sup.10)(R.sup.11); or W.sup.1 is selected from the group C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkynyl, O--C.sub.2 --C.sub.4 alkenyl and O--C.sub.2 --C.sub.4 alkynyl, each group optionally substituted with R.sup.9 ; PA1 n is 0, 1 or 2; and PA1 q is 0, 1, 2 or 3. PA1 A is a direct bond; PA1 Q is selected from the group phenyl and pyridyl, each ring substituted with R.sup.3, R.sup.4 and R.sup.5 ; PA1 R.sup.1 is selected from the group F and Cl in the 2-position; PA1 R.sup.2 is selected from the group H, F and Cl in the 6-position; and PA1 R.sup.3 is selected from the group C.sub.2 -C.sub.10 alkenyl optionally substituted with at least one member independently selected from R.sup.9 ; C.sub.2 -C.sub.10 alkynyl optionally substituted with at least one member independently selected from R.sup.9 ; and phenyl substituted with at least one member independently selected from W.sup.1. PA1 R.sup.3 is selected from the group C.sub.2 -C.sub.10 alkenyl optionally substituted with at least one member independently selected from R.sup.9 ; and PA1 R.sup.9 is selected from the group phenyl and pyridyl, each optionally substituted with at least one member independently selected from W. PA1 Z is O; PA1 R.sup.4 and R.sup.5 are H; and PA1 W is selected from halogen, CN, and OCHF.sub.2. PA1 R.sup.3 is selected from the group C.sub.2 -C.sub.10 alkynyl optionally substituted with at least one member independently selected from R.sup.9 ; and PA1 R.sup.9 is selected from the group phenyl and pyridyl, each optionally substituted with at least one member independently selected from W. PA1 Z is O; PA1 R.sup.4 and R.sup.5 are H; and PA1 W is selected from halogen, CN, and OCHF.sub.2. PA1 R.sup.3 is phenyl substituted with at least one member independently selected from W.sup.1 ; PA1 W.sup.1 is selected from the group C.sub.2 -C.sub.4 alkenyl and C.sub.2 -C.sub.4 alkynyl, O--C.sub.2 --C.sub.4 alkenyl and O--C.sub.2 --C.sub.4 alkynyl, each group optionally substituted with R.sup.9.
The oxazines and thiazines of this invention are not disclosed in this document.